Role Play
by QuidnamInferorum
Summary: Sam tries to convince the reader to tell Dean how she feels. Written for deansdirtylittlesecretsblog's Trope Challenge on tumblr. Prompt: Two people really like each other, but think the other doesn't like them, finally a middle man helps them get their act together.


"Okay, come on, let's try roleplaying."

"Wow, Sam, buy a girl dinner first."

The younger Winchester just rolled his eyes. "Look, anyone with half a brain knows how you feel about my brother, and I'm sick of it."

"Oh, good to know it's bothering you. It, obviously, hasn't affected me at all," Y/N frowned, pulling her feet down off of library table. She then turned away and curled in over the book she was reading, pointedly ignoring her friend, her back facing the war room.

Sam stood, walking around the table to kneel in front of his friend. He pushed the book down. "Look, Y/N, just…trust me on this. He's just as crazy about you as you are about him."

"Please," she frowned. "On what planet would he be into me?"

"Look, he's never gonna say anything, but you can."

Y/N closed her book and place it on the table beside him. "Sam, for the last time, I'm not telling him What'd be the point in that?"

"C'mon, Dean's gonna be gone for hours yet. Humor me."

Y/N huffed. "You're not gonna let this go, are you?"

He smiled innocently.

"Fine. You're Dean, I assume?"

"Wait, wait," Sam was grinning widely. He jumped up, pulling her along with him to stand. Sam cleared his throat and began his Dean impression, which included doing his best Blue Steel and pouting his lips comically. In a voice stupidly deep, he asked, "Hey sweetheart, what's—?"

Y/N immediately started snorting with laughter, their conjoined hands the only thing holding her up. " _Sam_!"

He laughed along with her. " _Fine_ ," he spoke as though this was a great disappointment for him. "Alright…what's up, Y/N?"

She huffed, her nerves taking over, even though it was only Sam. "W-Well…" she took a deep breath. "Um…" she trailed off into an awkward, tense silence.

Finally, Sam prodded her. "Is there _anything_ you want to tell me?"

She frowned. "Okay, so, like, Sam's an idiot and thinks that you like me—"

"Oh, nice."

"—and so I said I'd do this incredibly stupid thing. Dean…" she took a deep shuddering breath. "Okay. I'm in love with you. There. Happy?"

"What?" Sam's voice dropped an octave, which made her give Sam a taste of his own bitchface-flavored medicine. "Why would you be in love with me?"

"Really, Sam?" she whined.

"Humor me."

She frowned, glaring at their hands. "Fine. I love you because…because you can't sing but still do. Because you don't put yourself first unless I hold your feet to the fire. Because you tell the worst jokes at the worst times and they always get me. Because…because when you hold my hand I feel safer than I've ever felt in my whole entire life and…damn it, you make me feel like a bullshit damsel in a bullshit rom-com that you'd never admit to liking even though of _course_ you do—you're like a giant marshmallow under all that stupid tough guy 'oh I'm so cool and hardcore' bullshit, and—"

Sam dropped her hands, putting them on her shoulders. "Y/N, stop, you're rambling, we get it!"

She sighed heavily, putting her head in her hands. "Sorry, I just got nervous even though it was just you."

Then there was a beat of silence.

"Wait. _We_ get it?!" Y/N choked.

He smiled guiltily, which was all the answer she needed.

She whirled around to see Dean standing in the archway, his face bright red, bringing out the green in his wide open eyes.

"Oh…" Y/N felt her face get hot, and she felt herself die a little inside. "Fuck."

Sam patted her on the shoulder before walking across the long room to his brother. He patted the shorter man on the shoulder too, before walking out with a spring in his step.

Then they were alone.

And silent.

Finally, she began damage control. "Dean, look, I'm so sorry. I promise, this won't change anything between us. I'll back up and be out by nightfall if you really need, I just—"

"You love me?" Dean spoke quietly.

She laughed nervously. "I think that has been established."

Dean nodded, looking at her like she was a mirage that would vanish at any moment.

Then he moved.

He grabbed her face in his hands, angling her head perfectly to slant his lips over hers.

Sure that this had somehow turned into a waking dream, she grabbed ahold of the plaid flannel he had worn to the store, holding him close. The plaid was worn and warm and almost as soft at the lips that were moving hungrily against hers.

She vaguely felt the edge of the table they had been standing near begin digging into her upper thighs, and one hand let go of the shirt to fall back onto the table and hold herself up. One of his hands moved from her face down to the small of her back, holding her close enough to eliminate even an iota of space between them and she had to almost physically fight the urge to ride him right there.

Finally, when they had to breathe, they pulled away begrudgingly. Their foreheads fell lightly against each others, their breaths mingling.

His eyes were still closed, but hers were open, and she was memorizing every inch of his face: his flushed cheeks, his kiss-bruised lips, the dark eyelashes fanning across the cheeks that held all those freckles she fantasized about.

Her hand on the table came up to rest on his waist, her fingers lightly dancing along the strip of skin above his pants. The muscles jumped under her touch and she reveled in the physical sign that she got to him as much as he did her.

"Son of a bitch," Dean chuckled breathlessly.

"Agreed."

His other hand left her face to join its twin, holding her tightly. "Please tell me that this changes something and that you're not leaving."

She craned her neck to press a kiss to his lips. "This changes _everything_ and I'm not leaving as long as you want me here."

His eyes locked on hers. "How can you think I wouldn't want you?"

Any other time, she would've felt awkward; however, she was still riding the high of having Dean hold her like he was and his kiss, so she answered, "Have you met me?"

"Could say the same thing."

She scoffed. "Please."

"Seriously," he pulled away to shake his head. "I never would've thought you… _y'know_."

"Well, I think you heard me tell Sam _exactly_ how likely I thought you feeling anything for me was."

"Poor Sammy…he's had to listen to both of us complain about that," Dean realized.

"Probably why he told me you'd be out for hours yet and got me to say all that shit."

"Probably why he called me back because he said you needed me."

She flushed a little more, if that was possible. "So…you came for me?"

He shrugged. "Always would."

Y/N grinned wolfishly, slithering out of Dean's hold. She took his hand, pulling him towards the hallway. "C'mon, let's test that."

Dean's expression morphed into the one he used to pull in a bar, then agreed. "Oh, Sammy's gonna regret helping us."


End file.
